JP6097976B2 - 正孔輸送組成物ならびに関連するデバイスおよび方法(ii) - Google Patents
正孔輸送組成物ならびに関連するデバイスおよび方法(ii) Download PDFInfo
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- JP6097976B2 JP6097976B2 JP2013518772A JP2013518772A JP6097976B2 JP 6097976 B2 JP6097976 B2 JP 6097976B2 JP 2013518772 A JP2013518772 A JP 2013518772A JP 2013518772 A JP2013518772 A JP 2013518772A JP 6097976 B2 JP6097976 B2 JP 6097976B2
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- arylamine
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- 239000000203 mixture Substances 0.000 title claims description 154
- 230000005525 hole transport Effects 0.000 title claims description 151
- 238000000034 method Methods 0.000 title claims description 57
- 150000001875 compounds Chemical class 0.000 claims description 429
- 239000002904 solvent Substances 0.000 claims description 247
- 125000005264 aryl amine group Chemical group 0.000 claims description 138
- -1 arylamine compound Chemical class 0.000 claims description 95
- 239000000758 substrate Substances 0.000 claims description 92
- 238000004132 cross linking Methods 0.000 claims description 64
- 238000002347 injection Methods 0.000 claims description 63
- 239000007924 injection Substances 0.000 claims description 63
- 230000003381 solubilizing effect Effects 0.000 claims description 55
- 239000011248 coating agent Substances 0.000 claims description 32
- 238000000576 coating method Methods 0.000 claims description 32
- 238000010438 heat treatment Methods 0.000 claims description 30
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 28
- 150000004982 aromatic amines Chemical class 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 238000006116 polymerization reaction Methods 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 156
- 238000006243 chemical reaction Methods 0.000 description 133
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 116
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 116
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 102
- 239000010410 layer Substances 0.000 description 93
- 239000000976 ink Substances 0.000 description 91
- 230000015572 biosynthetic process Effects 0.000 description 74
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- 239000011541 reaction mixture Substances 0.000 description 67
- 238000003786 synthesis reaction Methods 0.000 description 65
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 64
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 63
- 229910052757 nitrogen Inorganic materials 0.000 description 63
- 239000010408 film Substances 0.000 description 56
- 239000000463 material Substances 0.000 description 55
- 239000000243 solution Substances 0.000 description 50
- 239000000047 product Substances 0.000 description 41
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 36
- 238000010992 reflux Methods 0.000 description 34
- 239000007787 solid Substances 0.000 description 33
- 238000005481 NMR spectroscopy Methods 0.000 description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 32
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 239000000741 silica gel Substances 0.000 description 30
- 229910002027 silica gel Inorganic materials 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 238000003756 stirring Methods 0.000 description 27
- 238000002390 rotary evaporation Methods 0.000 description 25
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 25
- 238000003818 flash chromatography Methods 0.000 description 22
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 22
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 20
- 125000004430 oxygen atom Chemical group O* 0.000 description 20
- 229910052717 sulfur Inorganic materials 0.000 description 20
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 18
- 238000000746 purification Methods 0.000 description 18
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 17
- 125000001072 heteroaryl group Chemical group 0.000 description 17
- 125000004434 sulfur atom Chemical group 0.000 description 17
- 229920002554 vinyl polymer Polymers 0.000 description 17
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 16
- 235000011089 carbon dioxide Nutrition 0.000 description 16
- 239000012043 crude product Substances 0.000 description 16
- 239000008367 deionised water Substances 0.000 description 16
- 229910021641 deionized water Inorganic materials 0.000 description 16
- 238000001914 filtration Methods 0.000 description 16
- CRUIOQJBPNKOJG-UHFFFAOYSA-N thieno[3,2-e][1]benzothiole Chemical group C1=C2SC=CC2=C2C=CSC2=C1 CRUIOQJBPNKOJG-UHFFFAOYSA-N 0.000 description 16
- 238000004809 thin layer chromatography Methods 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 229920000123 polythiophene Polymers 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 12
- 230000008020 evaporation Effects 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- 238000004770 highest occupied molecular orbital Methods 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- 125000006850 spacer group Chemical group 0.000 description 11
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 11
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 10
- XOCUXOWLYLLJLV-UHFFFAOYSA-N [O].[S] Chemical compound [O].[S] XOCUXOWLYLLJLV-UHFFFAOYSA-N 0.000 description 10
- 229920000547 conjugated polymer Polymers 0.000 description 10
- 235000019253 formic acid Nutrition 0.000 description 10
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 10
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 10
- 239000000499 gel Substances 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
- 101100030107 Phyllomedusa bicolor PLX-B gene Proteins 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 239000013058 crude material Substances 0.000 description 8
- 238000005695 dehalogenation reaction Methods 0.000 description 8
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- XAEPJWJMAQMSCO-UHFFFAOYSA-N 2-n,7-n-bis[3-(1,3-dioxolan-2-yl)phenyl]-2-n,7-n-bis(3-methylphenyl)-9,9-dioctylfluorene-2,7-diamine Chemical compound C1=C2C(CCCCCCCC)(CCCCCCCC)C3=CC(N(C=4C=C(C)C=CC=4)C=4C=C(C=CC=4)C4OCCO4)=CC=C3C2=CC=C1N(C=1C=C(C=CC=1)C1OCCO1)C1=CC=CC(C)=C1 XAEPJWJMAQMSCO-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 230000008863 intramolecular interaction Effects 0.000 description 7
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 125000001453 quaternary ammonium group Chemical group 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 0 CC1=*CC=*1 Chemical compound CC1=*CC=*1 0.000 description 6
- 238000004140 cleaning Methods 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- VYPYKCPWNPPBBX-UHFFFAOYSA-N 2-(3-bromophenyl)-1,3-dioxolane Chemical compound BrC1=CC=CC(C2OCCO2)=C1 VYPYKCPWNPPBBX-UHFFFAOYSA-N 0.000 description 5
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 238000010129 solution processing Methods 0.000 description 5
- 238000009987 spinning Methods 0.000 description 5
- 125000003107 substituted aryl group Chemical group 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- YIXLLBCNESJSFP-UHFFFAOYSA-N 2-n,7-n-bis(3-methylphenyl)-9,9-dioctylfluorene-2,7-diamine Chemical compound C=1C=C2C3=CC=C(NC=4C=C(C)C=CC=4)C=C3C(CCCCCCCC)(CCCCCCCC)C2=CC=1NC1=CC=CC(C)=C1 YIXLLBCNESJSFP-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000002800 charge carrier Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 4
- 125000000168 pyrrolyl group Chemical group 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- PWYVVBKROXXHEB-UHFFFAOYSA-M trimethyl-[3-(1-methyl-2,3,4,5-tetraphenylsilol-1-yl)propyl]azanium;iodide Chemical group [I-].C[N+](C)(C)CCC[Si]1(C)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PWYVVBKROXXHEB-UHFFFAOYSA-M 0.000 description 4
- 238000003828 vacuum filtration Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UDOWHURSZGVECO-UHFFFAOYSA-N 2-[3-(4-bromobutyl)phenyl]-1,3-dioxolane Chemical compound BrCCCCC1=CC=CC(C2OCCO2)=C1 UDOWHURSZGVECO-UHFFFAOYSA-N 0.000 description 3
- NUQRHTVEGHCJHN-UHFFFAOYSA-N 2-n,7-n-bis[3-(1,3-dioxolan-2-yl)phenyl]-9,9-dimethyl-2-n,7-n-dinaphthalen-1-ylfluorene-2,7-diamine Chemical compound C1=C2C(C)(C)C3=CC(N(C=4C=C(C=CC=4)C4OCCO4)C=4C5=CC=CC=C5C=CC=4)=CC=C3C2=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C(C=1)=CC=CC=1C1OCCO1 NUQRHTVEGHCJHN-UHFFFAOYSA-N 0.000 description 3
- FVYRJBRWEOGKEL-UHFFFAOYSA-N 2-n,7-n-bis[4-(1,3-dioxolan-2-yl)phenyl]-9,9-dimethyl-2-n,7-n-dinaphthalen-1-ylfluorene-2,7-diamine Chemical compound C1=C2C(C)(C)C3=CC(N(C=4C=CC(=CC=4)C4OCCO4)C=4C5=CC=CC=C5C=CC=4)=CC=C3C2=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C(C=C1)=CC=C1C1OCCO1 FVYRJBRWEOGKEL-UHFFFAOYSA-N 0.000 description 3
- ADQOJSQAQKEWET-UHFFFAOYSA-N 2-n,7-n-dinaphthalen-1-yl-2-n,7-n-diphenyl-9h-fluorene-2,7-diamine Chemical compound C1=C2CC3=CC(N(C=4C=CC=CC=4)C=4C5=CC=CC=C5C=CC=4)=CC=C3C2=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 ADQOJSQAQKEWET-UHFFFAOYSA-N 0.000 description 3
- APIUWSGRKQNGEB-UHFFFAOYSA-N 4,8-bis(3-methylphenyl)thieno[2,3-f][1]benzothiole Chemical compound CC1=CC=CC(C=2C=3SC=CC=3C(C=3C=C(C)C=CC=3)=C3SC=CC3=2)=C1 APIUWSGRKQNGEB-UHFFFAOYSA-N 0.000 description 3
- CBDUALHRIAANSR-UHFFFAOYSA-N 4-(4-bromobutyl)bicyclo[4.2.0]octa-1(6),2,4-triene Chemical compound BrCCCCC1=CC=C2CCC2=C1 CBDUALHRIAANSR-UHFFFAOYSA-N 0.000 description 3
- FVWKZHLLUHWJAM-UHFFFAOYSA-N 9,9-bis[4-(4-bicyclo[4.2.0]octa-1(6),2,4-trienyl)butyl]-2-n,7-n-bis(3-methylphenyl)-2-n,7-n-diphenylfluorene-2,7-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=C3C(CCCCC=4C=C5CCC5=CC=4)(CCCCC=4C=C5CCC5=CC=4)C4=CC(=CC=C4C3=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 FVWKZHLLUHWJAM-UHFFFAOYSA-N 0.000 description 3
- RRTQLQJTMGZTPV-UHFFFAOYSA-N 9,9-dimethyl-2-n,7-n-dinaphthalen-1-ylfluorene-2,7-diamine Chemical compound C1=CC=C2C(NC3=CC=C4C5=CC=C(NC=6C7=CC=CC=C7C=CC=6)C=C5C(C4=C3)(C)C)=CC=CC2=C1 RRTQLQJTMGZTPV-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000005484 gravity Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 238000000879 optical micrograph Methods 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000001376 precipitating effect Effects 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 125000003003 spiro group Chemical group 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- URMVZUQDPPDABD-UHFFFAOYSA-N thieno[2,3-f][1]benzothiole Chemical group C1=C2SC=CC2=CC2=C1C=CS2 URMVZUQDPPDABD-UHFFFAOYSA-N 0.000 description 3
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- H10K71/15—Deposition of organic active material using liquid deposition, e.g. spin coating characterised by the solvent used
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a single or double bond to nitrogen
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- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
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- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
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Families Citing this family (44)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107068914B (zh) | 2010-07-02 | 2020-05-08 | 日产化学工业株式会社 | 空穴传输组合物及相关器件和方法(i) |
WO2013006478A1 (en) | 2011-07-05 | 2013-01-10 | Plextronics, Inc. | Vertically phase-separating semiconducting organic material layers |
KR102008034B1 (ko) * | 2011-07-11 | 2019-08-06 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자용 화합물 |
US9978473B2 (en) | 2011-10-04 | 2018-05-22 | Nissan Chemical Industries, Ltd. | Doping methods for hole injection and transport layers |
JP5307954B1 (ja) * | 2011-11-07 | 2013-10-02 | 昭和電工株式会社 | 有機発光素子、その製造方法およびその用途 |
EP2610240A1 (en) * | 2011-12-28 | 2013-07-03 | Solvay Sa | Crosslinkable arylamine compounds |
EP2809706A4 (en) * | 2012-02-03 | 2016-01-13 | Univ Chicago | SEMICONDUCTOR POLYMERS |
TWI635111B (zh) | 2012-03-16 | 2018-09-11 | 馬克專利公司 | 共軛聚合物 |
EP2850668B1 (en) | 2012-05-15 | 2019-11-20 | Nissan Chemical Corporation | Hole transport materials including oled applications |
GB2509718A (en) * | 2013-01-09 | 2014-07-16 | Cambridge Display Tech Ltd | Method for forming a layer of an electronic device and appropriate precursor compounds |
EP3077477B1 (de) * | 2013-12-06 | 2018-02-28 | Merck Patent GmbH | Verbindungen und organische elektronische vorrichtungen |
JP6452063B2 (ja) * | 2014-02-25 | 2019-01-16 | 日本放送協会 | 正孔輸送材料 |
GB201412824D0 (en) * | 2014-07-18 | 2014-09-03 | Univ Manchester | Nanoparticles |
KR101631063B1 (ko) * | 2014-08-08 | 2016-06-16 | 경상대학교산학협력단 | 플루오렌 유도체를 포함하는 유기 반도체 화합물 및 이를 이용한 유기태양전지 |
KR20170045241A (ko) | 2014-08-21 | 2017-04-26 | 롬 앤드 하스 일렉트로닉 머트어리얼즈 엘엘씨 | 전자 장치용 산소 치환된 벤조클로부텐 유도 조성물 |
WO2016026122A1 (en) | 2014-08-21 | 2016-02-25 | Dow Global Technologies Llc | Benzocyclobutenes derived compositions, and electronic devices containing the same |
WO2016026123A1 (en) * | 2014-08-21 | 2016-02-25 | Dow Global Technologies Llc | Compositions comprising oxygen substituted benzocyclobutenes and dienophiles, and electronic devices containing same |
US10454036B2 (en) * | 2014-08-21 | 2019-10-22 | Dow Global Technologies Llc | Polymeric charge transfer layer and organic electronic device containing the same |
US10407581B2 (en) * | 2015-04-22 | 2019-09-10 | Nissan Chemical Industries, Ltd. | Non-aqueous compositions having sulfonated polythiophenes suitable for use in organic electronics |
CN107849377A (zh) * | 2015-07-17 | 2018-03-27 | 日产化学工业株式会社 | 适用于有机电子的包含准金属纳米颗粒的非水性油墨组合物 |
CN106412680B (zh) * | 2015-07-31 | 2021-01-22 | 中兴通讯股份有限公司 | 多屏控制方法及装置 |
US20180212180A1 (en) * | 2015-08-21 | 2018-07-26 | Dow Global Technologies Llc | Polymeric charge transfer layer and organic electronic device containing same |
EP3138858B1 (en) * | 2015-09-01 | 2019-10-30 | Samsung Electronics Co., Ltd. | Amino fluorene polymer and organic light-emitting device including the same |
GB2545626A (en) * | 2015-10-16 | 2017-06-28 | Lomox Ltd | Cross-linkable charge transport materials |
KR102126602B1 (ko) * | 2016-04-22 | 2020-06-24 | 주식회사 엘지화학 | 카바졸 유도체 및 이를 이용한 유기 발광 소자 |
KR102254298B1 (ko) * | 2016-08-23 | 2021-05-20 | 주식회사 엘지화학 | 카바졸 유도체 및 이를 이용한 유기 발광 소자 |
TWI732044B (zh) * | 2016-09-29 | 2021-07-01 | 日商住友化學股份有限公司 | 發光元件 |
CN109790105B (zh) * | 2016-10-06 | 2023-04-18 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
KR102673970B1 (ko) | 2016-10-13 | 2024-06-11 | 삼성디스플레이 주식회사 | 유기발광 표시장치 그 제조방법 |
US11165037B2 (en) | 2016-11-25 | 2021-11-02 | Lg Chem, Ltd. | Organic light-emitting diode |
CN107275362B (zh) | 2016-12-28 | 2020-10-09 | 上海天马有机发光显示技术有限公司 | 一种oled显示面板及包含其的电子设备 |
CN108794380B (zh) * | 2017-05-03 | 2021-07-23 | 中国科学院苏州纳米技术与纳米仿生研究所 | 用于电致发光器件的空穴传输材料 |
JP6975959B2 (ja) * | 2017-07-25 | 2021-12-01 | 国立大学法人山形大学 | アリールアミン誘導体、それを用いたホール輸送材料及び有機el素子 |
CN109851625B (zh) * | 2017-11-30 | 2021-05-25 | 湖北尚赛光电材料有限公司 | 一种苯并二噻吩的衍生物及其制备方法、应用和器件 |
KR102430143B1 (ko) | 2018-05-30 | 2022-08-08 | 주식회사 엘지화학 | 코팅 조성물, 이를 이용한 유기 발광 소자 및 이의 제조방법 |
CN112955489A (zh) | 2018-11-07 | 2021-06-11 | 默克专利有限公司 | 具有含胺基团的重复单元的聚合物 |
JP7330018B2 (ja) * | 2018-12-06 | 2023-08-21 | 住友化学株式会社 | 高分子化合物の製造方法 |
CN109768178B (zh) * | 2019-01-22 | 2021-03-30 | 京东方科技集团股份有限公司 | 有机电致发光器件、显示基板、显示装置 |
CN109912782B (zh) * | 2019-02-18 | 2020-06-02 | 中国科学院化学研究所 | 苯硼酸修饰的共轭聚合物及其制备方法与应用 |
CN110256358B (zh) * | 2019-07-12 | 2020-03-17 | 长春海谱润斯科技有限公司 | 一种胺类衍生物及其有机电致发光器件 |
KR20210074448A (ko) * | 2019-12-11 | 2021-06-22 | 삼성디스플레이 주식회사 | 유기 발광 소자 및 이를 포함하는 장치 |
CN111416050B (zh) * | 2020-04-16 | 2022-08-05 | 苏州欧谱科显示科技有限公司 | 一种空穴传输材料及其应用 |
JP2022132083A (ja) * | 2021-02-26 | 2022-09-07 | 住友化学株式会社 | 高分子化合物、組成物及び発光素子 |
US20240349587A1 (en) * | 2023-04-14 | 2024-10-17 | Kaunas University Of Technology | In-Situ crosslinking of 9,9' -spirobifluorene-based compounds for use in optoelectronic and/or in photoelectrochemical devices and manufacture thereof |
Family Cites Families (75)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5034296A (en) | 1989-04-03 | 1991-07-23 | Xerox Corporation | Photoconductive imaging members with fluorene polyester hole transporting layers |
US5055366A (en) | 1989-12-27 | 1991-10-08 | Xerox Corporation | Polymeric protective overcoatings contain hole transport material for electrophotographic imaging members |
US5149609A (en) | 1990-12-14 | 1992-09-22 | Xerox Corporation | Polymers for photoreceptor overcoating for use as protective layer against liquid xerographic ink interaction |
US5589320A (en) | 1993-07-21 | 1996-12-31 | Sumitomo Chemical Company, Limited | Polymeric fluorescent substance and organic electroluminescence devices using the same |
JP3463362B2 (ja) | 1993-12-28 | 2003-11-05 | カシオ計算機株式会社 | 電界発光素子の製造方法および電界発光素子 |
US5759709A (en) | 1994-03-10 | 1998-06-02 | Sumitomo Chemical Company, Limited | Polymeric fluorescent substance and organic electroluminescence device |
WO1997033193A2 (en) * | 1996-02-23 | 1997-09-12 | The Dow Chemical Company | Cross-linkable or chain extendable polyarylpolyamines and films thereof |
US5929194A (en) * | 1996-02-23 | 1999-07-27 | The Dow Chemical Company | Crosslinkable or chain extendable polyarylpolyamines and films thereof |
JP4442114B2 (ja) * | 2002-05-14 | 2010-03-31 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子及び表示装置 |
US6830833B2 (en) | 2002-12-03 | 2004-12-14 | Canon Kabushiki Kaisha | Organic light-emitting device based on fused conjugated compounds |
US7125633B2 (en) | 2002-12-16 | 2006-10-24 | Xerox Corporation | Imaging member having a dual charge transport layer |
EP1622955A2 (en) * | 2003-04-09 | 2006-02-08 | ZLX Techno Ltd. | Crosslinkable materials for organic light emitting devices and methods |
DE112004002221T5 (de) | 2003-11-17 | 2007-01-18 | Sumitomo Chemical Company, Ltd. | Vernetzbare substituierte Fluorenverindungen und konjugierte Oligomere oder Polymere, die darauf basieren |
JP4679136B2 (ja) * | 2003-12-22 | 2011-04-27 | 昭和電工株式会社 | 新規な重合性化合物、該重合性化合物の製造方法、該重合性化合物を含む重合性組成物及びその硬化物 |
KR100738219B1 (ko) * | 2003-12-23 | 2007-07-12 | 삼성에스디아이 주식회사 | 유기 전계 발광 소자용 중간층 형성 물질 및 이를 이용한유기 전계 발광 소자 |
US7365230B2 (en) | 2004-02-20 | 2008-04-29 | E.I. Du Pont De Nemours And Company | Cross-linkable polymers and electronic devices made with such polymers |
US7300731B2 (en) | 2004-08-10 | 2007-11-27 | E.I. Du Pont De Nemours And Company | Spatially-doped charge transport layers |
KR101269256B1 (ko) | 2004-09-24 | 2013-05-29 | 플렉스트로닉스, 인크 | 헤테로 원자를 갖는 위치 규칙적 폴리(3-치환 티오펜)를 포함하는 전기발광 소자 |
KR101314985B1 (ko) | 2005-02-10 | 2013-10-04 | 플렉스트로닉스, 인크 | 정공 주입/수송 층 조성물 및 장치 |
JP2006294319A (ja) * | 2005-04-07 | 2006-10-26 | Seiko Epson Corp | 有機発光素子の製造方法、有機発光素子、電子デバイスおよび電子機器 |
WO2007060854A1 (ja) * | 2005-11-28 | 2007-05-31 | Seiko Epson Corporation | 有機発光装置の製造方法、有機発光装置および電子機器 |
US8440324B2 (en) | 2005-12-27 | 2013-05-14 | E I Du Pont De Nemours And Company | Compositions comprising novel copolymers and electronic devices made with such compositions |
EP2412699A1 (en) | 2005-12-28 | 2012-02-01 | E.I. Du Pont De Nemours And Company | Compositions comprising novel compounds and electronic devices made with such compositions |
JP2007302886A (ja) * | 2006-04-14 | 2007-11-22 | Hitachi Chem Co Ltd | 有機エレクトロニクス用材料及びこれを用いた有機エレクトロニクス素子、有機エレクトロルミネセンス素子 |
EP2008500A4 (en) | 2006-04-18 | 2010-01-13 | Du Pont | HIGH ENERGY POTENTIAL BILOID COMPOSITIONS |
JP2009540574A (ja) | 2006-06-05 | 2009-11-19 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | Oled印刷の分野における有機活性材料を堆積するための液体組成物 |
WO2008073149A2 (en) | 2006-07-21 | 2008-06-19 | Plextronics, Inc. | Sulfonation of conducting polymers and oled, photovoltaic, and esd devices |
EP2069419A2 (en) | 2006-08-24 | 2009-06-17 | E.I. Du Pont De Nemours And Company | Hole transport polymers |
EP2074635A2 (en) | 2006-08-24 | 2009-07-01 | E.I. Du Pont De Nemours And Company | Crosslinkable hole transport polymers |
WO2008024380A2 (en) | 2006-08-24 | 2008-02-28 | E. I. Du Pont De Nemours And Company | Organic electronic devices |
KR100846590B1 (ko) * | 2006-11-08 | 2008-07-16 | 삼성에스디아이 주식회사 | 실란일아민계 화합물, 이의 제조 방법 및 이를 포함한유기막을 구비한 유기 발광 소자 |
KR100860411B1 (ko) | 2006-12-08 | 2008-09-26 | 한국전자통신연구원 | 멀티캐스트를 이용한 양방향 지역 광고 시스템 및 방법 |
US20080213624A1 (en) | 2007-02-28 | 2008-09-04 | E. I. Du Pont De Nemours And Company | Organic electronic device |
JP4946923B2 (ja) | 2007-03-07 | 2012-06-06 | 三菱化学株式会社 | 有機電界発光素子 |
US20080286566A1 (en) * | 2007-05-18 | 2008-11-20 | Shiva Prakash | Process for forming an organic light-emitting diode and devices made by the process |
CN101679207B (zh) | 2007-06-01 | 2014-05-28 | E.I.内穆尔杜邦公司 | 用于深蓝色发光应用的* |
WO2008150943A1 (en) | 2007-06-01 | 2008-12-11 | E.I. Du Pont De Nemours And Company | Hole transport materials |
JP2010534739A (ja) | 2007-07-27 | 2010-11-11 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 無機ナノ粒子を含有する導電性ポリマーの水性分散体 |
KR20100057074A (ko) * | 2007-09-26 | 2010-05-28 | 이데미쓰 고산 가부시키가이샤 | 유기 박막 트랜지스터 |
CN201178102Y (zh) * | 2007-10-11 | 2009-01-07 | 黄文成 | 一种有机电致发光器件 |
JP2011501360A (ja) | 2007-10-15 | 2011-01-06 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 溶液処理された電子デバイス |
EP2188858A1 (en) | 2007-10-23 | 2010-05-26 | E. I. du Pont de Nemours and Company | Ternary emissive layers for luminescent applications |
US8063399B2 (en) | 2007-11-19 | 2011-11-22 | E. I. Du Pont De Nemours And Company | Electroactive materials |
US8216753B2 (en) | 2007-12-13 | 2012-07-10 | E I Du Pont De Nemours And Company | Electroactive materials |
US8192848B2 (en) | 2008-01-11 | 2012-06-05 | E I Du Pont De Nemours And Company | Substituted pyrenes and associated production methods for luminescent applications |
KR100864140B1 (ko) * | 2008-01-11 | 2008-10-16 | 김종환 | 할로겐화 풀러렌 유도체를 이용한 유기 전계 발광 소자 |
JP5410679B2 (ja) | 2008-01-24 | 2014-02-05 | 昭和電工株式会社 | 有機エレクトロルミネッセンス素子およびその製造方法 |
KR20100111315A (ko) | 2008-02-01 | 2010-10-14 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 용액 처리된 전자 소자를 제조하기 위한 구조물 |
WO2009111339A1 (en) | 2008-02-29 | 2009-09-11 | Plextronics, Inc. | Planarizing agents and devices |
EP2257594B1 (en) | 2008-03-06 | 2014-11-12 | Plextronics, Inc. | Modified planarizing agents and devices |
US8692234B2 (en) * | 2008-04-02 | 2014-04-08 | Mitsubishi Chemical Corporation | Polymer compound, net-like polymer compound produced by crosslinking the polymer compound, composition for organic electroluminescence element, organic electroluminescence element, organic EL display, and organic EL lighting |
CA2720694C (en) | 2008-04-11 | 2017-05-23 | Plextronics, Inc. | Doped conjugated polymers, devices, and methods of making devices |
US8475938B2 (en) * | 2008-04-30 | 2013-07-02 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, lighting device and display device |
JP5644063B2 (ja) * | 2008-05-07 | 2014-12-24 | 三菱化学株式会社 | 有機電界発光素子用組成物、高分子膜、有機電界発光素子、有機elディスプレイ及び有機el照明 |
TW201005813A (en) | 2008-05-15 | 2010-02-01 | Du Pont | Process for forming an electroactive layer |
US8906520B2 (en) | 2008-06-09 | 2014-12-09 | Solvay Usa, Inc. | Sulfonated polythiophenes comprising fused ring repeat units |
US8225942B2 (en) | 2008-07-22 | 2012-07-24 | Trans Terra Corporation | Self-cleaning influent feed system for a wastewater treatment plant |
JP5417763B2 (ja) * | 2008-08-08 | 2014-02-19 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子用化合物 |
JP5491796B2 (ja) * | 2008-08-11 | 2014-05-14 | 三菱化学株式会社 | 電荷輸送性ポリマー、有機電界発光素子用組成物、有機電界発光素子、有機elディスプレイ及び有機el照明 |
JP5672681B2 (ja) * | 2008-09-18 | 2015-02-18 | 三菱化学株式会社 | 電荷輸送膜用組成物、有機電界発光素子、有機elディスプレイ及び有機el照明 |
KR101777551B1 (ko) | 2008-10-27 | 2017-09-11 | 닛산 가가쿠 고교 가부시키 가이샤 | 전하 주입 및 수송 층 |
JP5658161B2 (ja) | 2008-10-27 | 2015-01-21 | プレックストロニクス インコーポレーティッド | ポリアリールアミンケトン |
JP2010111750A (ja) * | 2008-11-05 | 2010-05-20 | Fujifilm Corp | 光吸収性組成物 |
US8283002B2 (en) | 2008-11-18 | 2012-10-09 | Plextronics, Inc. | Aminobenzene compositions and related devices and methods |
WO2010059240A1 (en) | 2008-11-21 | 2010-05-27 | Plextronics, Inc. | Doped interfacial modification layers for stability enhancement for bulk heterojunction organic solar cells |
US8278651B2 (en) | 2008-12-22 | 2012-10-02 | E I Du Pont De Nemours And Company | Electronic device including 1,7-phenanthroline derivative |
US20100187500A1 (en) | 2008-12-23 | 2010-07-29 | E.I.Du Pont De Nemours And Company | Carbon structures bonded to layers within an electronic device |
US8766239B2 (en) | 2008-12-27 | 2014-07-01 | E I Du Pont De Nemours And Company | Buffer bilayers for electronic devices |
US8785913B2 (en) | 2008-12-27 | 2014-07-22 | E I Du Pont De Nemours And Company | Buffer bilayers for electronic devices |
US8174000B2 (en) | 2009-02-11 | 2012-05-08 | Universal Display Corporation | Liquid compositions for inkjet printing of organic layers or other uses |
EP2417178A1 (en) | 2009-04-10 | 2012-02-15 | Plextronics, Inc. | Dehalogenation |
US8440785B2 (en) | 2009-06-30 | 2013-05-14 | Plextronics, Inc. | Compositions, methods and polymers |
CN102695707A (zh) * | 2009-12-28 | 2012-09-26 | 住友化学株式会社 | 化合物以及使用其的有机电致发光元件 |
JP5476234B2 (ja) * | 2010-06-30 | 2014-04-23 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子用材料、有機電界発光素子、及び有機電界発光素子の製造方法 |
CN107068914B (zh) | 2010-07-02 | 2020-05-08 | 日产化学工业株式会社 | 空穴传输组合物及相关器件和方法(i) |
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